Mayor Jerry Jennings looks over photographs representing over 20 years in office in his office at City Hall Wednesday Dec. 11, 2013, in Albany,NY. (John Carl D'Annibale / Times Union)

Mayor Jerry Jennings looks over photographs representing over 20...

A photo of Mayor Jerry Jennings and President Bill Clinton among the memorabilia collected over 20 years in office being packed up in Jennings' office in City Hall Wednesday Dec. 11, 2013, in Albany,NY. (John Carl D'Annibale / Times Union)

Mayor Jerry Jennings looks over memorabilia collected over 20 years in office to be boxed up and sent to the public archives at the Albany County Hall of Records at City Hall Wednesday Dec. 11, 2013, in Albany,NY. (John Carl D'Annibale / Times Union)

Mayor Jennings memorabilia collected over 20 years in office in the conference room at City Hall ready to be sent to the public archives at in the Albany County Hall of Records Wednesday Dec. 11, 2013, in Albany,NY. (John Carl D'Annibale / Times Union)

Mayor Jennings memorabilia collected over 20 years in office in the...

Mayor Jennings memorabilia collected over 20 years in office boxed up in the conference room at City Hall ready to be sent to the public archives at in the Albany County Hall of Records Wednesday Dec. 11, 2013, in Albany,NY. (John Carl D'Annibale / Times Union)

Mayor Jennings memorabilia collected over 20 years in office boxed...

Mayor Jennings memorabilia collected over 20 years in office boxed up in the conference room at City Hall ready to be sent to the public archives at in the Albany County Hall of Records Wednesday Dec. 11, 2013, in Albany,NY. (John Carl D'Annibale / Times Union)

The North Albany building at the corner of Broadway and Albany St. that once housed the Broadway Tavern, a bar owned by Mayor Jennings' father, Thursday Dec. 19, 2013, in Albany,NY. (John Carl D'Annibale / Times Union)

The North Albany building at the corner of Broadway and Albany St....

Mayor Jerry Jennings stands outside the North Albany building which once housed the Broadway Tavern, a bar owned by Jennings' father, Thursday Dec. 19, 2013, at the corner of Broadway and Albany St. in Albany, N.Y. (John Carl D'Annibale / Times Union)

All Jerry Jennings really needed to know to serve as mayor of Albany for 20 years he learned working behind the bar in his family's tavern at the corner of Broadway and Albany Street.

He was 15 when he started pulling quarter drafts of the two beers they kept on tap, Schaefer and Hedrick. The Schaefer brewery was a few blocks away, and that was a no-brainer. Hedrick's came from the South End and was owned by political boss Dan O'Connell. There were dark stories of what might happen to your establishment if you didn't order your kegs of Hedrick's and few dared tempt the tough, streetwise O'Connells, who ran a saloon on South Pearl Street.

Behind the bar, Jennings absorbed the rituals and mythology of the Democratic political machine, the Roman Catholic Church and the male realm. He learned the social compact that kept the planets aligned in the small, insular universe of the tight-knit Irish enclave.

It was a world view built upon tribal loyalty, and never forgetting where you came from. North Albany against the world, they were raised to believe.

He watched a ward leader and part-time bartender refuse to serve customers on Election Day until they confirmed that they had voted, and voted the Democratic ticket. The answer resulted in a fiver being slid across the bar in a quick, reflexive move.

As a bartender not yet old enough to drink legally, Jennings learned to keep a fresh head on pitchers and schooners and to keep his mouth shut during the rough-hewn repartee of workers from Niagara Mohawk's plant across the street. They kept the place afloat financially by claiming their stools at late afternoon and drinking "until they got cockeyed," Jennings recalled.

He made sure to pick up a quart of milk at the corner store for one of the regulars, an old, old guy named Goldie who had a bad ulcer. Jennings would spare the burn in the man's rotting gut by pouring Goldie's shot of Scotch into a glass of milk.

He heard sad tales of the broken lives of June Bug and Cheddar and Peg and a colorful cast of characters from the neighborhood known as Limerick, a crucible of heartache and humor, ruination and redemption.

Mostly, he learned to listen with an empathetic ear to the problems of downtrodden folks from the hardscrabble streets on which he came of age. Since he was a kid, the grimmer his circumstances became, the more he confronted sadness with a wisecrack or a joke. Humor became a defense mechanism, his default switch.

He has Albany etched into his DNA and pronounces the name of his beloved city with a native's inflection: "AWWW-bunny."

Coming up the hard way left wounds physical and psychological. Jennings pointed to a scar on his forehead between his eyebrows left from when he was a first-grader at School 20 and got into a fight with another kid. "He hit me with a brick and they brought me to the doctor," Jennings recalled while driving past the long-gone physician's office on Broadway. "He gave me a Band-Aid and told me to go back to school. He didn't believe in stitches."

That reminded Jennings of another story. One night, Peg came into the bar and proudly modeled a faux fur coat she bought at a thrift store that day. After several hours of drinking, she stumbled out the side door. Some time later, a patron came in and asked if anyone else had noticed the dead dog crumpled in a snowbank.

Jerry and a couple guys went out to revive Peg and carried to her apartment down the block.

It is an era long vanished into the vapors of memory, but before its smudged heart beat its last, it produced the city's 74th mayor.

The sign outside 1100 Broadway said Broadway Tavern. But nobody ever called it anything other than Jennings', a joint his grandfather opened in the 1940s. After his family sold the bar in 1974, it was converted into working-class apartments.

Jennings' bar was long, narrow and dark. Its pressed-tin ceiling was stained chestnut with a thick film of cigar and cigarette smoke. There was a shuffleboard in front, a dartboard in back and a small back room where they annexed troublemakers. "I'd throw them out the side door and they'd sneak back in the front," Jennings recalled.

The bar's glory years were in the mid-1960s, when a cook brought along a pet monkey. It was trained to carry out plates of burgers and sandwiches to customers who loved the unorthodox service and tipped generously.

It was an Irish bar, a place of epic stories that grew with each retelling, and ground zero for the Jennings clan. An uncle and their grandfather lived across the street, an aunt around the corner and the mayor's family — his father, mother, and Jerry's older brother and younger sister — lived in a first-floor, three-bedroom flat they rented at 2 Lawn Ave., six blocks from the bar.

Until they no longer did.

His dad was a heavy drinker. Late one night, he came from the bar and roused his wife and three young children from sleep. "He threw us out into the street," Jennings recalled. His voice was matter-of-fact. It was 1954, and Jerry, the middle child, was 6 years old. His parents' marriage of eight years was over.

The kids and their mom grabbed a few belongings and skulked down Broadway to Emmett Street, behind the bar, where an aunt lived. The four of them made do in a back room, sharing a fold-out couch and mattresses on the floor. It took about a year until their mom got on her feet and landed a job as a secretary with an insurance company.

They moved into a cheap apartment above a storefront at 246 Central Ave. Jerry and Joey shoveled sidewalks and hustled odd jobs to help their mom pay the rent.

"I guess it made us tough," Jennings said. "My mom always told us we were going to be all right. She made sure we got an education."

Jennings' dad was largely absent. The son found a role model in the Rev. John Fearey, pastor at Sacred Heart Church in North Albany. "Father Fearey watched out for me and the other kids in the neighborhood," Jennings said. "He kept us out of trouble. He taught us to work hard, play sports, stay in school and honor our families."

Jerry was a big kid, with beefy hands and a linebacker's build. As he grew into adolescence, the other kids stopped messing with him. He was a decent athlete and liked baseball best. He played Little League and Babe Ruth. He remembered one heartbreaking incident that summed up his childhood. He was playing a baseball game in Arbor Hill, the closest field to their apartment on Central Avenue. They couldn't afford a car, and because of her job and taking care of the kids his mom had never seen him play.

During the middle of a game one summer, Jennings watched a taxicab drive along the outfield and stop next to the bleachers behind home plate. It was such an odd sight that the umpire called time out. Players and spectators craned their necks to see Jennings' mom, brother and sister climb out of the cab.

Jennings' face flushed red as he stood at third base. He tried to look away as his mom waved excitedly. The adolescent shame was fleeting. What the action told him about a mother's love endured.

A dutiful son, Jennings worked hard to help supplement his mom's meager income.

He was hired as a temporary bellhop at the DeWitt Clinton Hotel across from the Capitol as a teenager. He got to know a group of senators who had a long-running poker game. Jerry became their runner and was summoned to replenish when they ran out of whiskey or cigars. When the senators heard he was about to be laid off, they flexed their political muscle: If Jerry goes, we go. Jennings kept the job.

The summer he turned 16, in addition to working at the bar he got a job as a stevedore at the Port of Albany. He was the only white guy on a longshoreman crew alongside a half-dozen African-American men. They unloaded wood pulp, grain, bananas, molasses and other cargo. Jennings thrived.

That experience gave him an easygoing, comfortable way with blacks that served him well as a teacher at Schuyler High, as vice principal at Albany High School, as a member of the Common Council and eventually as mayor of a city whose minority population increased during his tenure.

On a recent day, as Jennings walked the streets outside the Capital City Rescue Mission following a ribbon-cutting for new transitional apartments for homeless people, Jennings offered handclasps, shoulder squeezes, backslaps and headlocks to several black men, most of whom seemed down on their luck. It is hard to imagine any other white politician being able to pull this off with the naturalness and authenticity that Jennings displayed.

"Best thing that ever happened to Albany," said Carl Lovelady, unprompted, after seeing the mayor walking on his block. He is a retired state worker, a black man who lived on Lawn Avenue for the past 25 years, just up the street from where Jennings' dad threw his family out. The neighborhood has shifted from largely white and Irish households when Jennings grew up there to a majority of black and Hispanic families today.

Jennings put an arm on Lovelady's shoulder and asked about his family.

"He's very genuine," the mayor's sister said. "What you see is what you get with Jerry. Hardship made us stronger, and molded Jerry."

"He's the best retail politician I've ever seen," said R. Mark Sullivan, the former president of The College of Saint Rose in Albany. He became a close ally of Jennings and they collaborated on several projects, including an $8 million makeover of the city's rundown Hoffman Park in the South End into the Plumeri Complex in 2010. A 30-year lease agreement with the city gave the college much-needed athletic fields it lacked and offered city residents a first-rate athletic facility. The deal came together quickly. "He said let's do it for the kids," Sullivan recalled. "That was his standard refrain. He always cared deeply about the city's kids."

When Sullivan suffered a major stroke three years ago, Jennings visited him in the hospital every week. "He helped me through some of my darkest days," Sullivan said, recalling how Jennings knew most of the nurses and aides from his many years at Albany High and never failed to brighten the gloom with a joke.

Jennings' leadership style was intuitive, from the gut, and hands-on. He was a mayor who took calls at all hours and rushed to fires and homicide scenes. He understood that the biggest part of the job was showing up, and he did, often at two or three functions a night. He flashed a wide smile from behind a perpetually tan face and met well-wishers with his trademark, "Hiya, kid" or "Hey, babe" and "How ya doin'?"

"He's got a heart of gold and he's a big softie. He cries easily," said Bob Van Amburgh, a childhood friend from North Albany who's been Jennings' assistant for the past seven years. "I've never seen anyone who can connect with people the way he can."

Driving around the city with "Bobby" at the wheel and Jerry riding shotgun is a rolling comedy revue. They stopped to chat with a saxophone-playing Santa Claus. They rolled down the tinted windows of the mayor's SUV to shout a hello to anyone they knew walking along the street. They told childhood stories and tales from the bar. They argued over who was going to pay for lunch, two orders of takeout chicken soup and diet Pepsis, at Miranda's Deli on Columbia Street. They ended up splitting it.

Jennings is not a details guy. He left that to his alter ego, Deputy Mayor Phil Calderone, who spent the past 17 years reining in, shoring up and erecting a framework around the freewheeling ideas that Jennings tossed out on a daily basis after walking the streets, talking to residents at official events and schmoozing at political functions. They are a study in contrasts. Calderone is reserved and intense, with a lawyer's attention to minutiae. Calderone's office is meticulously neat and spartan, compared to Jennings' unkempt space and messy desk festooned with Post-it notes he writes to himself. Jennings is a great improviser and does not mind making it up as he goes along.

"He makes it fun to come to work every day because he always puts the city first," Calderone said. He conceded that Jennings occasionally can blow up at his staff, "but it's a passing storm."

It was never difficult to read the mayor because "he wears his heart on his sleeve," Calderone said.

Jennings has had a hard time letting go after he announced several months ago that he planned to retire at the end of his fifth term on Dec. 31, 2013.

Jennings told assistants to put off packing up 20 years of memorabilia until the final few weeks. They hastily stuffed 47 boxes with more than 120 plaques, dozens of honorary awards, hundreds of thank-you notes from schoolchildren and numerous hard hats, golden scissors and golden shovels from ribbon-cuttings and groundbreakings — the mayor's stock in trade.

"He's very emotional about this coming to an end," Van Amburgh said. "We've been doing our best to keep his mind off it."

"It's like our family is breaking up. It's really hard. He taught us all how to roll with the punches," said Sarah Samson, a special assistant to Jennings for the past six years after she was an intern while attending Union College.

"He always went the extra mile for people," said Pat Storm, a mayoral secretary for the past 27 years, starting with the late Thomas M. Whalen III. "I never worked for a greater guy."

Jennings has been roasted and toasted and feted by his staff, friends and city residents on his long goodbye tour, typically failing to fight back tears.

"I loved the people and I loved the job. I gave it my heart and soul," Jennings said, following a final staff meeting in which his voice was choked with emotion.

Jennings has never been good with endings. They sold the tavern not long after Jennings found his dad dead of a heart attack on the kitchen floor in his apartment above the bar. His dad was 52. Heavy drink and heavier smoking exacted its toll. The son did not have enough time to rebuild a relationship with his dad after many years of estrangement.

His mom died at 58 of a blood disorder.

His big brother Joey, who was 11 months older — "my Irish twin," Jennings called him — worked as a lawyer and served as Jennings' political strategist and campaign manager. "We were very close and I always looked up to him," Jennings said. "He had a great understanding of politics."

In a way, they fell into childhood roles, Joey the behind-the-scene brains and Jerry the out-front, swaggering brawn.

Jennings' brother died in 2008 of an aggressive form of stomach cancer. He was 61.

"Longevity is not in the Jennings genes," the mayor said last week in his ornate, wood-paneled City Hall office, where an oil painting of the city's first mayor, Pieter Schuyler, hangs above a fireplace.

In his final days in the hospital, his brother tried to convince Jennings to retire after his fourth term. But he decided he had unfinished business and stayed on for one more term. After his brother died, though, some of Jennings' passion for politics was gone, too.

Jennings is 65 years old and in good health following a tough recovery from knee replacement surgery 18 months ago. He has a generous Tier 1 state pension and his wife, Mary Ann, is a retired state worker who also has a pension. He has a son from his first marriage, Jerry, 43, an attorney. He wants to spend more time with his three grandchildren and maybe improve his golf game from a dismal 24 handicap when he golfs with his son and grandson. He likes to play Scrabble, Words with Friends and to sing at family functions. "But keep him away from the karaoke machine," his sister warned.

Jennings said he and his wife plan to travel. He is going to take some time to enjoy retirement, at his wife's urging. He vows to pitch in while she baby sits the grandkids. But he is keeping close at hand a "job offer card" with 25 names and numbers he has jotted down — feelers from lobbying firms, educational institutions and consulting outfits.

"I may not work for anyone," he said.

He'll try to lose the 25 pounds he gained as mayor and won't miss having to wear crisply pressed business suits every day. "I'll save a few thousand a year in dry cleaning," he said.

He joked at his final staff meeting that he planned to get back to serious tanning during regular trips to Florida because he heard people say he's been looking pale lately.

As Van Amburgh drove past the old Schuyler High School on Trinity Place in the South End — it's been converted to apartments — Jennings pointed out a corner classroom where he started his teaching career 40 years ago.

"Hey, Bobby. I used to sunbathe on that roof during my lunch hour," he said. "True story."